US3406164A - Disperse dyes of the monoazo series - Google Patents

Disperse dyes of the monoazo series Download PDF

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Publication number
US3406164A
US3406164A US520365A US52036566A US3406164A US 3406164 A US3406164 A US 3406164A US 520365 A US520365 A US 520365A US 52036566 A US52036566 A US 52036566A US 3406164 A US3406164 A US 3406164A
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parts
amino
dyes
formula
acetoxyethyl
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Altermatt Ruedi
Mueller Curt
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Sandoz AG
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Sandoz AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • R is lower alkyl
  • R is hydrogen, lower alkyl or lower alkoxy
  • R is alkylcarbonylalkyl, acyloxyalkyl, alkoxycarbonylalkyl or alkoxycarbonyloxyalkyl;
  • R is cyanoalkyl, acyloxyalkyl, alkoxycarbonylalkyl or alkoxycarbonyloxyalkyl; and R is alkoxy, acylamino, alkoxycarbonylamino, aralkoxycarbonylamino or aryloxycarbonylamino;
  • This invention relates to new dyes which are virtually insoluble in water and to the process for their production.
  • the dyes correspond to the formula 7 where:
  • R is a member selected from a group or radicals consisting of methyl, ethyl and halogeno-, cyano and hydroxylsubstituted methyl and ethyl,
  • R is a member selected from the group consisting of hydrogen, methyl, ethyl, methoxy and ethoxy,
  • R is a member selected from the group consisting of alkylcarbonylalkyl, unsubstituted and halogeno-, cyano-, alkoxy and acyl-substituted acyloxyalkyl, alkoxycarbonylalkyl and alkoxycarbonyloxyalkyl,
  • R is a member selected from the group consisting of cyanoalkyl, unsubstituted and ha1ogeno-, cyano-, alkoxyand acyl-substituted acyloxyalkyl, alkoxycarbonylalkyl and alkoxycarbonyloxyalkyl and 3,406,164 Patented Oct. 15, 1968
  • R is a member selected from the group consisting of alkoxy, unsubstituted and halogeno-, alkoxyaralkoxy and aryloxy-substituted acylamino, 'alkoxycarbonylamino, aralkoxycarbonylamino and aryloxycarbonylammo.
  • the said process for the production of these dyes consists in coupling a diazotized amine of formula OzN- NH:
  • Epecially preferred dyestuffs are of the formula OzN- N: N ⁇
  • R is a member selected from the group consisting ofliydrogen, methyl, ethyl, methoxy and ethoxy
  • R is a member selected from the group consisting of acetyl-ethyl, formyloxyethyl, methoxycarbonylethyl
  • each alkyl 1 of each alkyl and of each alkoxy is lower alkyl
  • each acyl is either formyl, lower alkanoyl or benzoyl
  • each ar'yl is phenyl.
  • French Patent 1,211,477 describes dyes which have the same coupling component and a similar diazo component. These dyes are less fast to thermofixation and sublimation than those of the present invention.
  • the aflinity and build-up properties of blue disperse dyes of the azo series are of special technical importance since blue is an essential component for the production of brown and grey combination shades.
  • the component dyes In combination dyeing the component dyes must exhaust the bath within wide limits in order to give dyeings of reproducible shade and depth.
  • Another advantage of blue dyes with good build-up properties is that they are the type suitable for producing heavy navy blue dyeings.
  • the coupling reaction is effected in an acid medium, which may be buttered if necessary, and with cooling, for example at temperatures of to C.
  • the new dyes thus obtained are excellent disperse dyes. It is of special advantage to convert them by known methods into dye preparations before use. This is effected by comminution to an average particle size of about 0.01 to microns or more particularly 0.1 to 5 microns. Comminution can be carried out in the presence of dispersants and fillers.
  • the dried dye can be ground with a dispersant, if necessary in the presence of fillers, or it can be kneaded in paste form with a dispersant and subsequently vacuum or jet dried.
  • the resulting preparations can beused for dyeing, pad ding or printing at long or short liquor ratios.
  • dyeing at long ratios it is general practice to use amounts of up to about grams of dye 'per lit're; for padding, up to about 150 grams, or preferably 0.1 to 100 grams, per litre; and for printing, up to about 150 grams per kilogram of print paste.
  • the liquor ratio may vary within wide limits, e.g. from about 1:3 to 1:200 or, preferably, 1:2 to 1:80.
  • the dyes build up excellently from aqueous dispersion on products made of synthetic or semisynthetic hydrophobic organic substances of high molecular weight.
  • linear aromatic polyester which in the main are polycondensation products of terephthalic acid and glycols, notably ethylene glycol, and are marketed under the registered trade names, Terylene, Diolene, Dacron, etc.
  • Polyester fibres can be exhaustion dyed in the presence of carriers at temperatures of about 80 to 125 C. or, in the absence of carriers, under pressure at about 100 to 140 C. These fibres can also be padded or printed with aqueous dispersions of the new dyes and paddings or prints fixed at about 140 C. to 230 C. with the aid of water vapour or air. In the optimum temperature range of 180 to 220 C. the dyes diffuse rapidly intopolyester fibreand do not then sublime, even when exposed for some length of time to these high temperatures, so that there is no inconvenient contamination of the dyeing and fixing equipment.
  • Cellulose diacetate is dyed preferably in the temperature range of about 65 to 80 C. and cellulose triacetate at temperatures up to about 115 C. The optimum pH region is 2 to 9 or, more particularly, 4 to 8.
  • the normal dispersing agents preferably those of anionic or nonionic character, can be used, either alone or in mixture. Often about 0.5 gram dispersing agent per litre of the dyeing medium is sufficient although larger amounts up to about 3 grams per litre can be used. Amounts in excess of 5 grams do not usually offer any further advantage.
  • Known anionic dispersing agents suitable for the process are, for example, the condensation products of naphthalene-sulphonic acids and formaldehyde, in particular dinaphthylmethane disulphonates, the esters of sulphonated succinic acid, Turkey red oil, the alkaline salts of the sulphuric acid esters of fatty alcohols, e.g.
  • suitable nonionic dispersing agents are the adducts of approximately 3- mols of ethylene oxide with alkyl phenyls, fatty alcohols or fatty amines, and their neutral sulphuric acid esters.
  • the normal thickening agents are used for padding and printing, e.g. modified or unmodified natural products, such as sodium alginates, British gum, gum Arabic, crystal gum, locust bean gum, gum tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starches, or synthetic products, such as polyacrylamides and polyvinyl alcohol.
  • modified or unmodified natural products such as sodium alginates, British gum, gum Arabic, crystal gum, locust bean gum, gum tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starches, or synthetic products, such as polyacrylamides and polyvinyl alcohol.
  • the dyeings obtained are extremely fast to heat (i.e. thermofixation, sublimation and pleating), gas fumes, cross dyeing, dry cleaning, chlorine, and to wet tests, such as water, washing and perspiration.
  • the dischargeability and reserve of wool and cotton are good.
  • the light fastness is outstanding even in pale shades, which makes the new dyes very suitable as components for the production of fashionable combination shades in pastel depths.
  • the dyes are stable to boiling and reduction at temperatures up to at least 220 C., showing particularly good stability at to 140 C.; this stability is not adversely affected either by the liquorv ratio or by the presence of. dyeing accelerants.
  • the blue members of this new group of dyes are suitable for combination with small amounts of red dyes for the production of low-cost navy blue dyeings which are fast to light, washing, perspiration, sublimation, pleating and thermofixation, and also for combination with red and yellow dyes for fast black dyeings. Combination dyeings with yellow dyes show an even tone-intone fade on exposure to light.
  • EXAMPLE 1 6.9 parts of powdered sodium'nitrite are added with vigorous stirring to 120 parts of concentrated sulphuric acid at 6070. After stirring for a further 10 minutes at 60 and cooling to 10, parts of glacial acetic acid are added at 10-15", followed by 26.1 parts of 2-amino- 3,5-dinitro-l-methylsulphonylbenzene and 100 parts of glacial acetic acid.
  • EXAMPLE 2 6.9 parts of finely divided sodium nitrite are added slowly with stirring to parts of concentrated sulphuric acid at 60-70", after which stirring is continued for 10 minutes at 60 with subsequent cooling to 20. At this temperature 26.1 parts of 2-amino-3,5-dinitro-l-methylsulphonylbenzene are added, and after stirring for a further 2 hours at 20-25 C. the resulting diazonium salt solution is run into a mixture of 33.6 parts of 1-N,N-di- (acetoxyethyl) amino 3 propionylaminobenzene, 100 parts of glacial acetic acid, 150 parts of ice and 10 parts of aminosulphonic acid.
  • the coupling reaction is finalized in an acid medium which may be buffered if necessary.
  • the precipitated dye is filtered off, washed free of acid, dried and recrystallized from alcohol. In the pure state it melts at The dye dyes synthetic fibres in bluish violet shades.
  • EXAMPLE 3 6.9 parts of powdered sodium nitrite are added with vigorous stirring to 120 parts of concentrated sulphuric acid at 60-70. Stirring is continued for 10 minutes at 7 8 60 and the bath cooled to 10", then 100 parts of glacial acetic acid are added at 10-15" followed by 26.1 parts of 2 amino 3,5-dinitro-l-methylsulphonylbenzene and 100 parts of glacial acetic acid. After stirring for another 2 hours the diazonium salt solution thus formed is run into a mixture of 33.3 parts of S-acetylamino-Z-ethoxy-l-N- Shade on Polyester fibre Greenis h blue.
  • Dyeing instructions 1 A mixture of 7 parts of the dye obtained according to Example 1, 4 parts of sodium dinaphthylmethanedisulphonate, 4 parts of sodium cetyl sulphate and 5 parts of anhydrous sodium sulphate is 00 ground in a ball mill for 48 hours to a fine powder. 2 parts of the powder are dispersed in a bath of 3000 parts of water containing 3 parts of a 30% solution of a highly sulphonated castor oil and parts of an emulsion of a chlorinated benzene. 100 parts of a fabric of Dacron (registered trademark) polyester fibre are introduced into the bath at 20-25 0, its temperature is raised to 95- l00 in about minutes and dyeing continued for 1 hour at this temperature. The fabric is then removed, rinsed, soaped for 15 minutes at 70 with a 0.1% solution of an 30 alkylphenylpolyglycol ether, rinsed again and dried. A greenish blue dyeing with excellent fastness properties is obtained.
  • Dacron registered trademark
  • Dyeing instructions 2 A mixture of 30 parts of the dye obtained according to Example 1, 40 parts of sodium dinapthylmethanedisulphonate, 50 parts of sodium cetyl sulphate and 50 parts of anhydrous sodium sulphate is ground in a ball mill for 48 hours to a fine powder. 4
  • Dyeing instructions 3 A mixture of 15 parts of the dye obtained according to Example 1, 20 parts of sodium dinaphthylmethanedisulphonate, 25 parts of sodium cetyl sulphate and 25 parts of anhydrous sodium sulphate is ground for 48 hours in a ball mill to a fine powder. 5 parts 50 of the powder are dispersed in 4000 parts of water. 100 parts of a scoured fabric of Arnel (registered trademark) cellulose triacetate fibre are entered and the bath raised slowly to 95-100". The fabric is dyed for about 1 hour at this temperature, then removed, rinsed, soaped 5 for 15 minutes at with a 0.1% solution of an alkylphenylpolyglycol ether, rinsed again and dried.
  • Arnel registered trademark
  • a violet dyeing is ob- 7O tained which has notably good fastness to gas fumes.
  • the dyes detailed in the following table are produced according to the procedure of Example 1 from a diazo tized amine of Formula II and a compound of Formula 111.
  • R is a member selected from the group consisting of methyl, halomethyl, cyanomethyl, hydroxymethyl, ethyl, haloethyl, cyanoethyl and hydroxyethyl;
  • R is a member selected from the group consisting of a hydrogen atom, methyl, ethyl, methoxy and ethoxy;
  • R is a member selected from the group consisting of alkylcarbonylalkyl, acyloxyalkyl, haloacyloxyalkyl, cyanoacyloxyalkyl, alkoxyacyloxyalkyl, acylacyloxy- :alkyl, alkoxycarbonylalkyl, haloalkoxycarbonylalkyl, cyanoalkoxycarbonylalkyl, alkoxyalkoxycarbonylalkyl, acylalkoxycarbonylalkyl, alkoxycarbonyloxyalkyl, haloalkoxycarbonylalkyl, cyanoalkoxycarbonyloxyalkyl, alkoxyalkoxycarbonyloxyalkyl and acylalkoxycarbonyloxyalkyl;
  • R is a member selected from the group consisting of cyanoalkyl, acyloxyalkyl, haloacyloxyalkyl, cyanoacyloxyalkyl, alkoxyacyloxyalkyl, acylacyloxyalkyl, alkoxycarbonylalkyl, haloalkoxycarbonylalkyl, cyanoalkoxycarbonylalkyl, alkoxyalkoxycanbonylalkyl, acylalkoxycarbonylalkyl, alkoxycarbonyloxyalkyl, haloalkoxycarbonyloxyalkyl, cyanoalkoxycarbonyloxyalkyl, alkoxyalkoxycarbonyloxyalkyl and acylalkoxycarbonyloxyalkyl; and
  • R is a member selected from the group consisting of alkoxy, acylamino, haloacylamino, alkoxyacylamino, aralkoxyacylamino, alkoxycarbonylamino, haloalkoxycarbonylamino, alkoxyalkoxycarbonylamino, aralkoxyalkoxycarbonylamino, aryloxyalkoxycarbonylamino, aralkoxycarbonylamino, haloaralkoxycarbonylamino, alkoxyaralkoxycarbonylamino, aralkoxyaralkoxycarbonylamino, aryloxyaralkoxycarbonylamino, aryloxycarbonylamino, haloaryloxycarbonylamino, alkoxyaryloxycanbonylamino, aralkoxyaryloxycarbonylamino, and aryloxyaryloxycanbonylamino;
  • S 02 io R is a member selected from the group consisting of methyl, ethyl, chloromethyl; cyanomethyl, bromomethyl, bromoethyl, chloroethyl, cyanoethyl and hydroxyethyl,
  • R is a member selected from the group consisting of hydrogen, methyl, ethyLmethoxy and ethoxy,
  • R is a member selected from the group consisting of acetylethyl, formyloxyethyl, methoxycarbonylethyl, ethoxycarbonylethyl, acetoxyethyl, chloroand brornoacetoxyethyl, cyanoacetoxyethyl, methoxyacetoxyethyl, ethoxyacetoxyethyl, propyloxyacetoxyethyl, acetoxyacetoxyethyl, methoxycarbonyloxyethyl, ethoxycarbonyloxyethyl, chloroand bromo-ethoxycarbonyloxyethyl, propylcarbonyloxyethyl, acetoacetoxyethyl, methoxycarbonyloxyethyl, ethoxycarbonyloxyethyl, chloroand bromo-ethoxycarbonyloxyethyl, propylcarbonyloxyethy
  • R is a member selected from the group consisting of cyanoethyl, formyloxyethyl, rnethoxycarbonylethyl, ethoxycarbonylethyl, acetoxyethyl, chloroand brorno-acetoxyethyl, cyanoacetoxyethyl, methoxyacetoxyethyl, ethoxyacetoxyethyl, propyloxyacetoxyethyl, acetoxyacetoxyethyl, methoxycar bonyloxyethyl, ethoxyc-arbonyloxyethyl, chloroand bromo-ethoxycarbonyloxyethyl, propylcarbonyloxyethyl, acetoacetoxyethyl, methoxycarbonyloxyethyl, ethoxycarbonyloxyethyl, chloroand bromo-ethoxycarbonyloxyethyl, propylcarbon
  • R is a member selected from the group consisting of methoxy, ethoxy, formylarnino, acetylamino, chloroacetylamino, methoxylacetylamino, ethoxyacetylamino, phenyloxyacetylamino, methoxycarbonylamino, ethoxycarbonylarnino, chloroand bromo-ethoxycarbonylamino, methoxymethoxycarbonylamino, ethoxymethylcarbonylamino, phenylmethylcarbonylamino, tertiary butylcarbonylamino, phenyloxyacetylamino, phenylmethoxycarbonylamino, phenylmethoxymethoxycarbonylamino, propionylamino, monoand dichloropropionylamino, ibromopropionylamino, butyrylamino, monoand di-chloro-butyrylamin
  • the dye according to claim 2 of the formula N02 C 2C 3 /CHzCHzO C 0 CH3 OzN- N N- N ⁇ l CIHCH OCOCHCS SOzCHa NHCOCH3 5.
  • the dye according to claim 2 of the formula NO: OCH3 i CH2CH20COCH3 OzN- N N N CH CHzOC OCH; SO CH; NHCOCEzCHz 6.
  • the dye according to claim 2 of the formula 7 The dye according to claim 2 of'the formula OCH2CH3 No;

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US520365A 1965-01-14 1966-01-13 Disperse dyes of the monoazo series Expired - Lifetime US3406164A (en)

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CH51965A CH455085A (de) 1965-01-14 1965-01-14 Verfahren zur Herstellung von Dispersionsfarbstoffen der Monoazoreihe

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US520396A Expired - Lifetime US3428622A (en) 1965-01-14 1966-01-13 Water-insoluble phenyl azo phenyl dyes

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US (2) US3406164A (enrdf_load_stackoverflow)
BE (1) BE674798A (enrdf_load_stackoverflow)
CH (2) CH455085A (enrdf_load_stackoverflow)
DE (2) DE1644342A1 (enrdf_load_stackoverflow)
FR (1) FR1463508A (enrdf_load_stackoverflow)
GB (2) GB1125570A (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510470A (en) * 1966-05-02 1970-05-05 Eastman Kodak Co Phenyl-azo-analine dyes
US3522234A (en) * 1966-10-06 1970-07-28 Sandoz Ag Monoazo dyes of the azobenzene series
US3692769A (en) * 1970-02-18 1972-09-19 Max A Weaver Azo compounds containing an arylsulfonyl phenyl diazo component
US4046757A (en) * 1968-10-18 1977-09-06 Sandoz Ltd. 2-Optionally substituted alkyl-and phenylsulfonylphenyl-azo-phenyl dyes and a process for their synthesis
US4085099A (en) * 1973-04-13 1978-04-18 Produits Chimiques Ugine Kuhlmann Water-insoluble nitrophenylazophenyl compounds containing a terminal --N--(C2)n --O--CO-- or --CO--O--CH2 --CH2 --C3 F5 group
US4119624A (en) * 1972-06-08 1978-10-10 Imperial Chemical Industries Limited Disperse monoazo dyestuffs
US4123293A (en) * 1975-03-07 1978-10-31 Hitachi, Ltd. Method of providing semiconductor pellet with heat sink
US5973127A (en) * 1996-06-25 1999-10-26 Basf Aktiengesellschaft Monoazo dyes substituted by haloalkylcarbamate and sulphonylfluoride groups

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4042580A (en) * 1970-05-06 1977-08-16 Sandoz Ltd. Phenylazophenyl dyes having an alkoxyacylamino group on the coupling component radical
CH584269A5 (enrdf_load_stackoverflow) * 1973-12-21 1977-01-31 Sandoz Ag

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2111300A (en) * 1936-02-10 1938-03-15 Firm J R Geigy S A Monoazo-dyestuffs and their manufacture
US2249749A (en) * 1939-11-14 1941-07-22 Eastman Kodak Co Azo compounds and material colored therewith
US2891942A (en) * 1955-07-13 1959-06-23 Saul & Co Water-insoluble monoazo dyestuffs
GB856348A (en) * 1956-07-25 1960-12-14 Westminster Bank Ltd Improvements in or relating to water-insoluble monoazo dyestuffs containing carboxylic ester groups
US3178405A (en) * 1956-07-25 1965-04-13 Merian Ernest Water-insoluble monoazo dyestuffs
US3268507A (en) * 1962-08-10 1966-08-23 Bayer Ag Water-insoluble monoazo dyestuffs
US3342803A (en) * 1963-02-21 1967-09-19 Ciba Ltd Water-insoluble monoazo-dyestuffs

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2111300A (en) * 1936-02-10 1938-03-15 Firm J R Geigy S A Monoazo-dyestuffs and their manufacture
US2249749A (en) * 1939-11-14 1941-07-22 Eastman Kodak Co Azo compounds and material colored therewith
US2891942A (en) * 1955-07-13 1959-06-23 Saul & Co Water-insoluble monoazo dyestuffs
GB856348A (en) * 1956-07-25 1960-12-14 Westminster Bank Ltd Improvements in or relating to water-insoluble monoazo dyestuffs containing carboxylic ester groups
US3178405A (en) * 1956-07-25 1965-04-13 Merian Ernest Water-insoluble monoazo dyestuffs
US3268507A (en) * 1962-08-10 1966-08-23 Bayer Ag Water-insoluble monoazo dyestuffs
US3342803A (en) * 1963-02-21 1967-09-19 Ciba Ltd Water-insoluble monoazo-dyestuffs

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510470A (en) * 1966-05-02 1970-05-05 Eastman Kodak Co Phenyl-azo-analine dyes
US3522234A (en) * 1966-10-06 1970-07-28 Sandoz Ag Monoazo dyes of the azobenzene series
US4046757A (en) * 1968-10-18 1977-09-06 Sandoz Ltd. 2-Optionally substituted alkyl-and phenylsulfonylphenyl-azo-phenyl dyes and a process for their synthesis
US3692769A (en) * 1970-02-18 1972-09-19 Max A Weaver Azo compounds containing an arylsulfonyl phenyl diazo component
US4119624A (en) * 1972-06-08 1978-10-10 Imperial Chemical Industries Limited Disperse monoazo dyestuffs
US4085099A (en) * 1973-04-13 1978-04-18 Produits Chimiques Ugine Kuhlmann Water-insoluble nitrophenylazophenyl compounds containing a terminal --N--(C2)n --O--CO-- or --CO--O--CH2 --CH2 --C3 F5 group
US4123293A (en) * 1975-03-07 1978-10-31 Hitachi, Ltd. Method of providing semiconductor pellet with heat sink
US5973127A (en) * 1996-06-25 1999-10-26 Basf Aktiengesellschaft Monoazo dyes substituted by haloalkylcarbamate and sulphonylfluoride groups

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Publication number Publication date
FR1463508A (fr) 1966-12-23
BE674798A (enrdf_load_stackoverflow) 1966-05-16
GB1125570A (en) 1968-08-28
US3428622A (en) 1969-02-18
DE1644343B2 (de) 1974-07-11
DE1644342A1 (de) 1970-12-10
CH498907A (de) 1970-11-15
GB1128176A (en) 1968-09-25
CH455085A (de) 1968-04-30
DE1644343C3 (de) 1975-03-20
DE1644343A1 (de) 1971-05-06

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